Hydrochloric Acid → 2-Amino-4-methoxybenzoic acid

HRID 617121Notes

Reaction equation

HRID 617121 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4](N)=[O:5].Cl.[OH-:14].[Na+]>>[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:14])=[O:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 140230022-Amino-4-methoxybenzamide

Product 1

HCID 3510102-Amino-4-methoxybenzoic acid

Procedure

A solution of 27.4 g (0.165 mol) of 2-amino-4-methoxybenzamide in 500 mL of 1N sodium hydroxide was stirred and heated under reflux for 18 hours. After the reaction mixture had cooled to room temperature the solution was brought to pH 6-7 with 0.5N HCl. A white precipitate formed which was collected by vacuum filtration. The crystals were rinsed with water and dried overnight at 100° C. The product amounted to 23.9 g. An analytical sample (mp 176-178° C.) was obtained by recrystallization from ethyl acetate.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 hours
  3. customA white precipitate formed which
  4. filtrationwas collected by vacuum filtration
  5. washThe crystals were rinsed with water
  6. customdried overnight at 100° C
  7. customAn analytical sample (mp 176-178° C.) was obtained by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-675984d37fee4c66b5d8a3c04ab04ac6
Source dataset
uspto-grants-1999_09
Patent number
US05948775

Reaction notes

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